New Formulas for Organozincate Chemistry

Autor: Masanobu Uchiyama, Yoshinori Kondo, Nobuko Yokoyama, Takao Sakamoto, Mitsuyoshi Kameda, Osamu Mishima, Minako Koike
Rok vydání: 1998
Předmět:
Zdroj: Journal of the American Chemical Society. 120:4934-4946
ISSN: 1520-5126
0002-7863
DOI: 10.1021/ja973855t
Popis: As a new type of zincate, we designed various new organozinc derivatives, Me3Zn(R)Li2 (R = Me, CN, SCN), which could be prepared in situ from lithium trimethylzincate and anion species such as methyllithium, lithium cyanide, and lithium thiocyanate. We investigated the reactivities of these zincates toward the halogen (or tellurium)−zinc exchange, Michael addition, carbozincation, and epoxide ring opening reactions. On the basis of their excellent chemical yields and chemoselectivities, these species were considered to be differentiated from ordinary triorganozincates, R3ZnLi. We also discuss the structure of the newly designed zincates using 1H NMR/Raman/in situ FTIR/extended X-ray absorption fine structure (EXAFS) spectroscopic and the density-functional theory (DFT) theoretical studies. All results strongly support the fact that these newly designed zincates are a new category of zincate species. This observation is also identical with the fact that newly designed zincates have a higher and unique reac...
Databáze: OpenAIRE